I think it would've been easy to throw the #Mastodon logo at some print-on-demand website and be done with it, but I've always wanted Mastodon merch to be something bespoke, something you'd genuinely want to keep for years. This is why I chose the difficult path: Manually finding suppliers, prototyping, ordering in advance and distributing through our own shop. It's a lot of work, which is why it tends to happen as individual "drops" rather than a continuous, all year round stock.
I boost, therefore I am.
There have been a few requests for more serious merch items (so not "Live, laugh, federate" and "I write alt text", though those definitely have their place). @Amelia Rochko and I brainstormed a few messages we could put on t-shirts and I want to see how well they resonate with folks. Again, very non-committal.